Though, talking to a stranger through their window doesn't help with the whole idea of sneaking, thus I can understand why OP would be confused by lack of wing use (i.e. if they are going to ignore discretion anyway, why not fly to undertake the operation faster?)

Maybe Charity is acting as a diversion. It would appear she volunteered for that. She might be using some of Pandora's old tricks which worked quite well among a sex starved population of angels, but I'm not so sure it will be as effective in an all girl school that encourages sexual activity.

Sort of this. Charity might want to go undercover by dressing up as a demoness so she can search around without being discovered. Hence, she'll tie up this girl and replace her...

I've considered that option and if she has to do some unspeakable things with another girl to get that uniform "it's all part of the mission" is what she'll tell Prudence. ;)

Also, hurr hurr, Naomi is a butt monkey for no reason other than there *needed* to be one,

To be fair Naomi has been pretty much a butt monkey since day one. Despite being the only person to see that there was something strange going on in Teddy's house she was always something of a Cassandra type figure with nobody believing her. That and her being Gaby's victim and the random scenes of her and Prudence usually fleeing some kind of monster continued the tone.

So really Prudence jumping on her head is just another relatively minor example of that.

True enough. Though, my point was more about how here it was unnecessary slapstick against a character that didn't deserve it, at least, shouldn't have any more additions to series of abuse she endures, even if this a fairly minor example.

Charity's divinity has been depleted so hers might not work so well. It actually makes more sense to climb in since they're trying to sneak into Tartarus Academy and seeing people with angelic wings is bound to ring some alarm bells.

Though, talking to a stranger through their window doesn't help with the whole idea of sneaking, thus I can understand why OP would be confused by lack of wing use (i.e. if they are going to ignore discretion anyway, why not fly to undertake the operation faster?)

Maybe Charity is acting as a diversion. It would appear she volunteered for that. She might be using some of Pandora's old tricks which worked quite well among a sex starved population of angels, but I'm not so sure it will be as effective in an all girl school that encourages sexual activity.

Personally, I'd think a distraction would work better at the front door, or at least somewhere that isn't directly beneath the breach team's ascent point. While I don't think Charity's actions are a part of a distraction plan, there isn't definitive evidence to entirely dismiss it as a possibility.